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The earliest settlement in Brooklyn Township, outside of the Ohio City area, took place in 1814 on the bluff south of the Big Creek valley at the present intersection of Pearl and Broadview Roads. After incorporating in 1838 as the Village of Brighton (e.g., "Brooklyn-Brighton Bridge"), the area was re-absorbed by the Township one year later and remained in that status until 1889, when the Village of South Brooklyn was incorporated. South Brooklyn lost municipal status in 1905 when it was annexed to Cleveland. The western and southeastern portions of Old Brooklyn became part of Cleveland when Brooklyn Township and portions of the Village of Brooklyn Heights were annexed in 1917 and 1927, respectively.

The trip between South Brooklyn and Cleveland was shortened in 1905 when the Pearl Road street-car line was extended south across the Big Creek valley. The area now known as Brookside Park was purchased in 1894 by Cleveland's Park Board and became the permanent home of the Cleveland Zoo in 1908, when the Zoo was relocated from the University Circle area.

During the late 1880's, the area around Schaaf Road (now known as South Hills) began to develop as one of the first in the Midwest to utilize greenhouses for the growing of vegetables. By the 1920's the neighborhood was one of the nation's leading producers of greenhouse vegetables, with over 100 acres under glass. Today only a handful of greenhouses remain, with some former greenhouse sites providing prime site for the development of contemporary housing.

Commercial development in Old Brooklyn intensified during the 1920's particularly along Pearl, Broadview and State Roads. Newer shopping plazas were developed more recently in the neighborhood at the intersections of Memphis and Fulton, Broadview and Brookpark, and Pearl and Brookpark. Residential development continued at a significant pace from the early part of the century through the 1960's. During the late 1980's, residential development experienced a resurgence, particularly in the South Hills and Jennings Road areas. Today, housing values in Old Brooklyn remain among the highest in Cleveland.

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